The TT Pro League is the Trinidad and Tobago professional league for association football clubs. It is the country's primary football competition and serves as the top division in the Trinidad and Tobago football league system. Contested by ten clubs, the league is one of the world's few football leagues that does not operate on an automatic system of promotion and relegation. Seasons run from September to May, with teams playing 18 games each totaling 90 games in the season. Most games are played in the evenings of Fridays and Saturdays, with a few games played during weekday evenings. Pro League clubs also play in other competitions, such as the FA Trophy, League Cup, TOYOTA Classic, Goal Shield, and Pro Bowl against domestic clubs from other divisions; and against clubs from other countries in the CFU Club Championship, the CONCACAF League and the CONCACAF Champions League.
The Trinidad and Tobago Pro Bowl, or commonly known as the Digicel Pro Bowl for sponsorship reasons, is a knockout football tournament for teams in the TT Pro League. The competition is played during May following the conclusion of the Pro League season. The Pro Bowl began without a sponsor during the competitions's first two years. It was not until 2006, when Courts began providing monetary prizes, that the tournament had its first sponsor. Following a pullout by Courts after three years, Digicel became the new branding partner of the competition. The prize money for the winner, as announced by TT Pro League CEO Dexter Skeene, is determined by the players, the clubs and the communities. With this programme the communities are expected to adopt the clubs and pledge their support to them during the tournament. The prize money will be the amount received from gate receipts and TT$100,000, courtesy of tournament sponsors Digicel.
The 2010–11 Trinidad and Tobago FA Trophy was the 81st season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. Joe Public entered as the tournament's defending champion, who defeated W Connection in the 2009 final. The tournament commenced on 17 November 2010, with 32 teams competing in single elimination matches and concluded on 25 January 2011.
The 2008 Trinidad and Tobago FA Trophy was the 79th season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. The tournament took place at the conclusion of the 2008 season. Joe Public entered as the tournament's defending champion. The tournament began on 3 December, with 32 teams competing in single elimination matches.
The 2011–12 TT Pro League season was the thirteenth season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of eight teams contested the league, with Defence Force as the defending champions. The season began on 9 September 2011 and ended on 29 March 2012 with the crowning of W Connection as the league champion. Dexter Skeene, Pro League CEO, announced on 11 February 2011 that by aligning its seasons with those of the major leagues in Europe, the Pro League will afford the opportunity to further link culture with sport to harness and develop the talent of people in Trinidad and Tobago.
The 2012–13 TT Pro League season was the fourteenth season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of eight teams contested the league, with W Connection the defending champions. The season began on 14 September 2012 and ended on 10 May 2013 with the crowning of Defence Force as the league champion.
The 2012 Trinidad and Tobago Charity Shield was the inaugural edition of the Charity Shield, which was a football match that opened the 2012–13 TT Pro League season. The match was played at Manny Ramjohn Stadium in Marabella on 8 September 2012, between the winners of the previous season's Pro League and Pro Bowl competitions. The match was contested by the 2012 Digicel Pro Bowl winners, Defence Force, and the champions of the 2011–12 Pro League, W Connection. The Savonetta Boys won the match 2–0 with goals from Shahdon Winchester and Joevin Jones, who was later named the Man of the Match.
The Trinidad and Tobago Charity Shield is the country's annual football match contested between the champions of the previous TT Pro League season and the holders of the Pro Bowl. If the Pro League champions also won the Pro Bowl, then the league runners-up provide the opposition. Often seen as a "glorified friendly", which ranks below the FA Trophy and First Citizens Cup, the fixture is a recognised football Super Cup. The match is sponsored by Digicel and is therefore officially known as the Digicel Charity Shield.
The 2012–13 Trinidad and Tobago FA Trophy was the 83rd season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. Caledonia AIA entered as the tournament's defending champion, who defeated Defence Force 1–0 in the 2011–12 final at Manny Ramjohn Stadium. The tournament began on 5 December 2012 with 36 teams competing in single elimination matches and concluded on 1 March 2013 with the crowning of the cup winners.
The 2013 Trinidad and Tobago Charity Shield was the second edition of the Charity Shield, which is a football match that opened the 2013–14 Pro League season. The match was played on 6 September 2013, between the winners of the previous season's TT Pro League and Pro Bowl competitions. The match was a rematch of the inaugural Charity Shield contested by the 2013 Pro Bowl winners, W Connection, and the champions of the 2012–13 Pro League, Defence Force.
The 2012 Trinidad and Tobago Goal Shield was the third season of the Lucozade Sport Goal Shield, which is a knockout tournament competition for Trinidad and Tobago teams competing in the TT Pro League. North East Stars entered as the Goal Shield holders after defeating San Juan Jabloteh 1–0 in the 2010 final. Continuing from previous seasons, the competition not only allowed the winner and runner-up healthy purses at the end of the tournament, but more so give an added incentive for more goals to be scored throughout the tournament. In particular, the winner of the competition was awarded TT$20,000 plus an additional TT$3,000 for every goal scored in the final, TT$2,000 for every goal in the semifinals, and TT$1,000 for each goal scored in the quarterfinals. Whereas, the runner-up was awarded TT$10,000 plus TT$1,500 for every goal scored in the final, TT$1,000 for every goal in the semifinals, and TT$500 for each goal scored in the quarterfinals.
The 2014 Trinidad and Tobago Goal Shield was the fifth season of the Lucozade Sport Goal Shield, which is a knockout tournament competition for Trinidad and Tobago teams competing in the TT Pro League. W Connection entered as the cup holders having defeated North East Stars 4–3 in a penalty shootout in the 2013 final. Continuing from previous seasons, the competition not only allowed the winner and runner-up healthy purses at the end of the tournament, but more so give an added incentive for more goals to be scored throughout the tournament. In particular, the winner of the competition was awarded TT$30,000 plus an additional TT$3,000 for every goal scored in the final, TT$2,000 for every goal in the semifinals, and TT$1,000 for each goal scored in the quarterfinals. Whereas, the runner-up was awarded TT$10,000 plus TT$1,500 for every goal scored in the final, TT$1,000 for every goal in the semifinals, and TT$500 for each goal scored in the quarterfinals.
The 2013 Trinidad and Tobago Goal Shield was the fourth season of the Lucozade Sport Goal Shield, which is a knockout tournament competition for Trinidad and Tobago teams competing in the TT Pro League. Caledonia AIA entered as the cup holders having defeated Defence Force 3–1 in the 2012 final. Continuing from previous seasons, the competition not only allowed the winner and runner-up healthy purses at the end of the tournament, but more so give an added incentive for more goals to be scored throughout the tournament. In particular, the winner of the competition was awarded TT$20,000 plus an additional TT$3,000 for every goal scored in the final, TT$2,000 for every goal in the semifinals, and TT$1,000 for each goal scored in the quarterfinals. Whereas, the runner-up was awarded TT$10,000 plus TT$1,500 for every goal scored in the final, TT$1,000 for every goal in the semifinals, and TT$500 for each goal scored in the quarterfinals.
The 2013 Trinidad and Tobago Pro Bowl was the ninth season of the Digicel Pro Bowl, which is a knockout football tournament for Trinidad and Tobago teams competing in the TT Pro League. For the third consecutive season, the Pro Bowl concluded the Pro League calendar. Additionally, for the second year the winner of the Pro Bowl was invited to compete in the Digicel Charity Shield to open the 2013–14 Pro League season. Defence Force entered as the Pro Bowl holders having defeated Caledonia AIA by a score of 5–2 in the 2012 final in Hasely Crawford Stadium. The competition commenced on 17 May with all eight Pro League teams competing in single elimination beginning in the quarterfinals and concluded on 29 May with the final.
The 2014 Trinidad and Tobago Pro Bowl is the tenth season of the Digicel Pro Bowl, which is a knockout football tournament for Trinidad and Tobago teams competing in the TT Pro League. For the fourth consecutive season, the Pro Bowl concluded the Pro League calendar. Additionally, for the third year the winner of the Pro Bowl was invited to compete in the Digicel Charity Shield to open the 2014–15 Pro League season. W Connection entered as the Pro Bowl holders having defeated North East Stars by a score of 4–3 in a penalty shootout after the match ended in 0–0 in regulation during the 2013 final in Hasely Crawford Stadium. The competition commenced on 2 May with all nine Pro League teams competing in single elimination beginning with the qualifying round and concluded on 23 May with the final.
The 2015–16 TT Pro League season is the seventeenth season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of ten teams are contesting the league, with Central FC the defending champions from the 2014–15 season. The season began on 25 September 2015 and concluded on 21 May 2016 with the crowning of Central FC as the league champion.
Leston Peter Paul is a Trinidadian professional footballer who plays as a midfielder for Memphis 901 in the USL Championship.
The 2017 Trinidad and Tobago FA Trophy was the 86th season of the FA Trophy, which is the oldest football competition for teams in Trinidad and Tobago. North East Stars entered as the tournament's defending champion, who defeated W Connection 5-4 on penalties after a 0–0 in the 2014–15 final at Ato Boldon Stadium. The tournament began on 16 September with 64 teams competing in single elimination matches and will conclude with the final on 8 December. W Connection won their 5th FA Trophy after beating Police 3-1 in the final at the Ato Boldon Stadium.
The 2017 Trinidad and Tobago League Cup was the eighteenth season of the First Citizens Cup, which is the league cup competition for Trinidad and Tobago teams competing in the TT Pro League. Defence Force entered as the cup holders having defeated Ma Pau Stars by a score of 1–0 in the 2016 final. First Citizens Bank changed the slogan to "Where Winners Reign" due to the amount of money that the winner of the tournament would obtain. Teams were drawn into numbers with respect to their position in the 2017 TT Pro League at the time of the draw. It means that teams from 7–10 in the league enter at the play-offs, while from 1–6 enter at the quarterfinal stage. W Connection were crowned 8-time champions after defeating Defence Force in the final.
The 2018 TT Pro League season is the 20th season of the TT Pro League, the Trinidad and Tobago professional league for association football clubs, since its establishment in 1999. A total of ten teams are contesting the league, with North East Stars the defending champions from the 2017 season.
